Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-06-07
1999-07-06
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548479, C07C 2900
Patent
active
059199482
ABSTRACT:
A novel ligand having the Formula 1 structure has proved remarkably successful in the amination of butadiene monoepoxide, which is a potentially desirable substrate for an asymmetric synthesis providing access to each enantiomer of vinylglycinol. ##STR1## This and other ligands described are useful for chiral induction of bond forming reactions with an epoxide substrate.
REFERENCES:
patent: 4209468 (1980-06-01), Shulman
patent: 4705895 (1987-11-01), Okano et al.
Morrison and Masler, J. Org. Chem., 39:2, pp. 270-272 (1974).
Masuda and Stille, J. Am. Chem. Soc., 100:1, pp. 268-272 (1978).
LaFont et al., J. Chem. Research (S), 234, p. 117 (1982).
Riley, J. Organomet. Chem., 234, pp. 85-97 (1982).
MacNeil et al., J. Am. Chem. Soc., 103, pp. 2273-2280 (1981).
Fryzuk and Bosnich, J. Am. Chem. Soc., 99:19, pp. 6262-6267 (1977).
Roberts and Wild, J. Am. Chem. Soc., 101:21, pp. 6254-6260 (1979).
Bergstein et al., Synthesis, 76, pp. 76-78 (1981).
Juge et al., Tetrahedron Letters, 31:44, pp. 6357-6360 (1990).
Imamoto et al., J. Am. Chem. Soc., 112, pp. 5244-5252 (1990).
Knowles et al., J. Am. Chem. Soc., 97:9, pp. 2567-2568 (1975).
Fukuda et al., Tetrahedron Letters, 31:49, pp. 7185-7188 (1990).
Onuma et al., Chem. Letters, pp. 905-908 (1979).
Achiwa, J. Am. Chem. Soc., 98:25, pp. 8265-8266 (1976).
Beck and Menzel, J. Organomet. Chem., 133, pp. 307-310 (1977).
Kagen and Dang, J. Am. Chem. Soc., 94:18, pp. 6429-6433 (1972).
Aviron-Violet et al., J. Mol. Catal., 5, pp. 41-50 (1979).
Dang et al., J. Organomet. Chem., 91, pp. 105-115 (1975).
Glaser et al., Tetrahedro Letters, 52, pp. 4639-4642 (1977).
Kreuzfeld and Dobler, React. Kinet. Catal. Lett., 16:2-3, pp. 229-232 (1981).
Pracejus and Pracejus, J. Mol. Catal., 24, pp. 227-230 (1984).
Samuel et al., Nouv. J. Chim, 5:1, pp. 15-20 (1981).
Lauer et al., J. Organomet. Chem., 177, pp. 309-312 (1979).
Tanaka et al., Chem. Lett., pp. 1115-1118 (1975).
Alario et al., J. Chem. Soc., Chem. Com., pp. 202-203 (1986).
Takaya et al., Org. Syn., 67, pp. 20-32 (1989).
Grubbs and DeVries, Tetrahedron Letters, 22, pp. 1879-1880 (1977).
Trost and Murphy, Organometallics, 4, pp. 1143-1145 (1985).
Tamao et al., Tetrahedron Letters, 16, pp. 1389-1392 (1977).
Miyano et al., Chem. Lett., pp. 729-730 (1980).
Miyano et al., Bull. Chem. Soc. Jpn., 57, pp. 2171-2176 (1984).
Uehara et al., Chem. Lett., pp. 441-444 (1983).
Hayashi et al., Bull. Chem. Soc. Jpn., 53, pp. 1138-1151 (1980).
Hayashi and Kumada, Acc. Chem. Res., 15, pp. 395-401 (1982).
Johnson et al., J. Mol. Catal., 12, pp. 37-40 (1981).
Petit et al., Nouv. J. Chim., 7:10, pp. 593-596 (1983).
Pracejus and Pracejus, Tetrahedron Letters, 39, pp. 3497-3500 (1977).
Fiorini et al., J. Mol. Catal., 4, pp. 125-134 (1978).
Consiglio and Waymouth, Chem. Rev., 89, pp. 257-276 (1989).
Noyori and Kitamura, "Enantioselective Catalysis with Metal Complexes. An Overview," in Modern Synthetic Methods, vol. 5, Scheffold, ed., Springer-Verlag: Berlin, pp. 115-198 (1989).
Noyori, Chem. Soc. Rev., 18, pp. 187-208 (1989).
Ojima et al., Tetrahedron Letters, 45:22, pp. 6901-6939 (1989).
Blystone, Chem. Rev., 89:8, pp. 1663-1679 (1989).
Brunner, "Enantioselective Syntheses with Optically Active Transition Metal Catalysts," chapter in The Chemistry of the Metal-Carbon Bond, vol. 5, Hartley, ed., and John Wiley & Sons: New York, pp. 109-146 (1989).
Brunner, Synthesis, pp. 645-653 (1988).
Merlic, "Transition Metal Mediated Asymmetric Allylic Alkylations," chapter 2 in Molybdenum Catalyzed Allylic Alkylations, Ph. D. Dissertation, University of Wisconsin, Madison, pp. 780-79 (1988).
Kitamura et al., Tetrahedron Letters, 28:40, pp. 4719-4720 (1987).
Trost et al., J. Am. Chem. Soc., 110, pp. 621-622 (1988).
Trost and Van Vranken, J. Am. Chem. Soc., 113: pp. 6317-6318 (1991).
Fiorini and Giongo, J. Mol. Catal., 5, pp. 303-310 (1979).
Trost and Van Vranken, Angewandte Chemie, 31:2, pp. 228-230 (1992).
Trost et al., J. Am. Chem. Soc., 114, pp. 9327-9343 (1992).
Whitesell, Chem. Rev., 89, pp. 1581-1590 (1989).
Bunt Richard C.
Trost Barry M.
Gerstl Robert
The Board of Trustees of the Leland Stanford Junior University
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